Acetonitrile → 3-Cyclopentyl-3-oxopropanenitrile

HRID 2109924Notes

Reaction equation

HRID 2109924 reaction equation
[H-].[Na+].[CH:3]1([C:8]([O:10]C)=O)[CH2:7][CH2:6][CH2:5][CH2:4]1.[C:12](#[N:14])[CH3:13]>C1COCC1.C(OCC)(=O)C.Cl>[CH:3]1([C:8](=[O:10])[CH2:13][C:12]#[N:14])[CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

7

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 78365Methyl cyclopentanecarboxylate

Product 1

HCID 135921183-Cyclopentyl-3-oxopropanenitrile

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
71 °C

Procedure

To a suspension of NaH (2.75 g, 68.7 mmol) in THF (15 mL) at 70° C. was added dropwise a solution of methyl cyclopentanecarboxylate (8.00 g, 62.4 mmol) and anhydrous acetonitrile (3.91 mL, 74.9 mmol) in THF (5 mL). The mixture was stirred for 16 h at 70-72° C., cooled to rt, and diluted with ethyl acetate and aqueous HCl. The organic layer was washed with water and brine and dried (MgSO4). Removal of the solvent provided 3-cyclopentyl-3-oxopropanenitrile, which was used without further purification.

Workup

  1. temperaturecooled to rt
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-013c4eb20f934454977c39d5c2b2e112
Source dataset
uspto-grants-2009_04
Patent number
US07517878B2

Reaction notes

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